[ CAS No. 192702-79-7 ] {[proInfo.proName]}

Name: 192702-79-7|(3-Fluoro-4-methylphenyl)methanol|98%
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Quality Control of [ 192702-79-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 192702-79-7 ]

Product Details of [ 192702-79-7 ]

CAS No. :	192702-79-7	MDL No. :	MFCD01631533
Formula :	C₈H₉FO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UUVJAGTYIVYFOS-UHFFFAOYSA-N
M.W :	140.15	Pubchem ID :	2774590
Synonyms :

Calculated chemistry of [ 192702-79-7 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	37.49
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	1.5
Log Po/w (WLOGP) :	1.89
Log Po/w (MLOGP) :	2.3
Log Po/w (SILICOS-IT) :	2.56
Consensus Log Po/w :	2.05

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.03
Solubility :	1.3 mg/ml ; 0.00929 mol/l
Class :	Soluble
Log S (Ali) :	-1.53
Solubility :	4.11 mg/ml ; 0.0293 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.87
Solubility :	0.191 mg/ml ; 0.00136 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.18

Safety of [ 192702-79-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P271-P302+P352-P305+P351+P338-P362-P403+P233-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 192702-79-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 192702-79-7 ]
Downstream synthetic route of [ 192702-79-7 ]

[ 192702-79-7 ] Synthesis Path-Upstream 1~2

1
[ 192702-79-7 ]
[ 177756-62-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 11, p. 1634 - 1647

2
[ 192702-79-7 ]
[ 170572-49-3 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 11, p. 1634 - 1647

[ 192702-79-7 ] Synthesis Path-Downstream 1~22

1
[ 350-28-7 ]
[ 192702-79-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;	Step 1: (3-fluoro-4-methylphenyl)methanol [0282] To a stirred suspension of LiAIH4 (0.51 g, 12.9 mmol) in dried THF (10 mL) was added dropwise a solution of <strong>[350-28-7]3-fluoro-4-methylbenzoic acid</strong> (2.02 g, 12.9 mmol) in dried THF at 0 C under N2 atmosphere. After stirring overnight at room temperature, the mixture was quenched by addition of Na2S04 10H2O. After stirring at r.t. for 30 min, the solid was removed by filtration, and the filtered mass was extracted with EtOAc. The combined organic phases were washed with brine, dried Na2S04, and concentrated in vacuo. The residue was purified by column chromatography over silica gel (hexane/EtOAc = 5/1) to afford the title compound as a colorless oil (1.21 g, 67%). Eta NM (400 MHz, CDCI3) delta 7.16 (t, J = 8.0 Hz, 1H), 7.04-7.01 (m, 2H), 4.65 (s, 2H), 2.26 (d, J = 1.6 Hz, 3H).

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647
[2]Patent: WO2016/100349,2016,A2 .Location in patent: Paragraph 0282

2
[ 192702-79-7 ]
[ 177756-62-6 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647

3
[ 192702-79-7 ]
[ 170572-49-3 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647

4
[ 192702-79-7 ]
3-Fluoro-N-(4-methanesulfonyl-phenyl)-4-methyl-benzamidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / 1.) CH₂Cl₂, -70 deg C, 1.5 h, 2.) CH₂Cl₂, from -70 deg C to RT, 3 h 2: pyridine; hydroxylamine hydrochloride / 1.) RT, 15 min, 2.) toluene, reflux, 4 h 3: trimethylaluminum / 1.) toluene, a) 0 deg C - RT, b) RT, 3.5 h, 2.) toluene, 70 deg C - 75 deg C, 17 h

Reference： [1]Khanna, Ish K.; Weier, Richard M.; Yu, Yi; Xu, Xiang D.; Koszyk, Francis J.; Collins, Paul W.; Koboldt, Carol M.; Veenhuizen, Amy W.; Perkins, William E.; Casier, Jacquelen J.; Masferrer, Jaime L.; Zhang, Yan Y.; Gregory, Susan A.; Seibert, Karen; Isakson, Peter C. [Journal of Medicinal Chemistry, 1997, vol. 40, # 11, p. 1634 - 1647]

5
[ 192702-79-7 ]
2-(3-fluoro-4-methylphenyl)-1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / 1.) CH₂Cl₂, -70 deg C, 1.5 h, 2.) CH₂Cl₂, from -70 deg C to RT, 3 h 2: pyridine; hydroxylamine hydrochloride / 1.) RT, 15 min, 2.) toluene, reflux, 4 h 3: trimethylaluminum / 1.) toluene, a) 0 deg C - RT, b) RT, 3.5 h, 2.) toluene, 70 deg C - 75 deg C, 17 h 4: sodium hydrogencarbonate / isopropyl alcohol / 20 h / 75 - 80 °C 5: toluene-4-sulfonic acid / toluene / 72 h / Heating

6
[ 192702-79-7 ]
[ 1026237-46-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / 1.) CH₂Cl₂, -70 deg C, 1.5 h, 2.) CH₂Cl₂, from -70 deg C to RT, 3 h 2: pyridine; hydroxylamine hydrochloride / 1.) RT, 15 min, 2.) toluene, reflux, 4 h 3: trimethylaluminum / 1.) toluene, a) 0 deg C - RT, b) RT, 3.5 h, 2.) toluene, 70 deg C - 75 deg C, 17 h 4: sodium hydrogencarbonate / isopropyl alcohol / 20 h / 75 - 80 °C

Yield	Reaction Conditions	Operation in experiment
		R.13.b 3-Fluoro-4-methylbenzaldehyde b) 3-Fluoro-4-methylphenylmethanol To a mixture of 0.176 g (4.6 mmol) of LiAlH4and 14 mL of Et2O, 0.5 g (4.6 mmol) of the preceding product dissolved in 28 mL of Et2O was added at 0 °C and under an argon atmosphere, and the mixture was stirred at room temperature for 2 h. 0.28 mL of H2O, 0.6 mL of THF, 0.29 mL of 15 % NaOH, 0.8 mL of H2O and Na2SO4were successively added. After stirring for 10 min the mixture was filtered, washed with Et2O and concentrated, affording 0.3 g of a crude product which was directly used in the next step (93%). 1H-NMR (300 MHz, CDCl3δ TMS): 2.1 (broad s, 1 H), 2.26 (s, 3 H), 4.62 (s, 2 H), 7.0 (m, 3 H).

8
[ 351-54-2 ]
[ 192702-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran	19.1 (3-fluoro-4-methylphenyl)methanol Step 1 (3-fluoro-4-methylphenyl)methanol 3-fluoro-p-anisaldehyde (12.5 g, 81.1 mmol) was dissolved in 100 ml THF. Under N2 a solution of diisobutylalumium hydride (100 ml, 1M in THF) was added at 0° C. over 30 min. The reaction was stirred for 30 min and quenched with 250 ml 1N HCl solution. The resulting mixture was stirred for 15 min and filtered through a short column of Celite. The product was extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried with MgSO4, and concentrated to give a viscous oil in 11.6 g. This product was used without further purification. NMR spectra of the product were consistent for the proposed structure.
	In tetrahydrofuran	20.1 (3-fluoro-4-methylphenyl)methanol Step 1 (3-fluoro-4-methylphenyl)methanol 3-fluoro-p-anisaldehyde (12.5 g, 81.1 mmol) was dissolved in 100 ml THF. Under N2 a solution of diisobutylalumium hydride (100 ml, 1M in THF) was added at 0° C. over 30 min. The reaction was stirred for 30 min and quenched with 250 ml 1 N HCl solution. The mixture was stirred for 15 min and filtered through a short column of Celite. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried with MgSO4, and concentrated to give an oil in 11.6 g. This product was used without further purification. NMR spectra of the product were consistent for the proposed structure.

Reference： [1]Current Patent Assignee: GASIECKI; SCHRETZMAN; RUSSELL (unclear); CHANDRAKUMAR; CHEN; NAGARAJAN; HUFF; DESAI; YU (inventors); ROGERS (inventors); KHILEVICH; KHANNA; FUN LU; WANG (inventors); WENDT (inventors); ASATSU-DK INC; PENNING; PFIZER INC - US6531494, 2003, B1
[2]Current Patent Assignee: GASIECKI; SCHRETZMAN; RUSSELL (unclear); CHANDRAKUMAR; CHEN; NAGARAJAN; HUFF; DESAI; YU (inventors); ROGERS (inventors); KHILEVICH; KHANNA; FUN LU; WANG (inventors); WENDT (inventors); ASATSU-DK INC; PENNING; PFIZER INC - US6531494, 2003, B1

9
[ 192702-79-7 ]
[ 147542-00-5 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride	19.2 4-(chloromethyl)-2-fluoro-1-methylbenzene Step 2 4-(chloromethyl)-2-fluoro-1-methylbenzene Thionyl chloride (0.892 g, 7.5 mmol) was added to a solution of the product of STEP 1 (1.0 g, 6.4 mmol) in 10 ml ether dropwise at 0° C. After 30 min, the reaction was quenched with crushed ice carefully, and diluted with H2O. The product was extracted with ether. The organic layer was washed with saturated NaHCO3 solution, brine, dried with Na2SO4, and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/9) to give a colorless liquid in 10.5 g. NMR spectra of the product were consistent for the proposed structure.

10
[ 192702-79-7 ]
[ 1422528-66-2 ]
[ 1422528-67-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: phosphorus tribromide / dichloromethane / 1 h / 20 °C 2.1: sodium azide / dimethyl sulfoxide / 16.5 h / 0 - 20 °C 3.1: trifluorormethanesulfonic acid / toluene / 3 h / 20 °C 3.2: 0.08 h / 20 °C

Reference： [1]Tummatorn, Jumreang; Thongsornkleeb, Charnsak; Ruchirawat, Somsak; Gettongsong, Tanita [Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467]

11
[ 192702-79-7 ]
[ 1422528-60-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: phosphorus tribromide / dichloromethane / 1 h / 20 °C 2: sodium azide / dimethyl sulfoxide / 16.5 h / 0 - 20 °C

Reference： [1]Tummatorn, Jumreang; Thongsornkleeb, Charnsak; Ruchirawat, Somsak; Gettongsong, Tanita [Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467]

12
[ 192702-79-7 ]
4-(bromomethyl)-2-fluoro-1-methylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus tribromide In dichloromethane at 20℃; for 1h;
	With phosphorus tribromide In diethyl ether at 0 - 20℃;	7.2 Step-2: Preparation of 4-(bromomethyl)-2-fluoro-l-methylbenzene To a stirred solution of (3-fluoro-4-methylphenyl)methanol (1 g, 7.16 mmol, 1 eq) in diethyl ether (20 mL) was slowly added PBn (2.3 g, 8.57 mmol, 1.2 eq) at 0 °C and the mixture was stirred at RT. The reaction was monitored by TLC. After completion, the mixture was quenched with a solution of saturated aqueous NaHCC (150 mL) and extracted with EtOAc (200 mL). The organic layer was washed with water (75 mL c 2), brine (50 mL), dried over NaaSCL, filtered and concentrated under reduced pressure to afford the title compound, which was used without further purification. Analytical data: LC-MS 203 [M+H]+.

Reference： [1]Tummatorn, Jumreang; Thongsornkleeb, Charnsak; Ruchirawat, Somsak; Gettongsong, Tanita [Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467]
[2]Current Patent Assignee: NUVATION BIO INC; SPARCBIO LLC (SUNNYVALE) - WO2020/113094, 2020, A1 Location in patent: Page/Page column 70-71

13
[ 192702-79-7 ]
C₁₃H₁₄FNO₂ [ No CAS ]
C₁₃H₁₄FNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: phosphorus tribromide / dichloromethane / 1 h / 20 °C 2: sodium azide / dimethyl sulfoxide / 16.5 h / 0 - 20 °C 3: trifluorormethanesulfonic acid / toluene / 3 h / 20 °C

Reference： [1]Tummatorn, Jumreang; Thongsornkleeb, Charnsak; Ruchirawat, Somsak; Gettongsong, Tanita [Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467]

14
N-(((3S,4R)-3-fluoropiperidin-4-yl)methyl)-[1,2,4]triazolo[4,3-a]pyrazin-8-amine dihydrochloride [ No CAS ]
[ 530-62-1 ]
[ 192702-79-7 ]
(3S,4R)-3-fluoro-4-methylbenzyl 4-(([1,2,4]triazolo[4,3-a]pyrazin-8-ylamino)methyl)-3-fluoropiperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: 1,1'-carbonyldiimidazole; (3-fluoro-4-methylphenyl)methanol In dimethyl sulfoxide at 20℃; for 1h; Stage #2: N-(((3S,4R)-3-fluoropiperidin-4-yl)methyl)-[1,2,4]triazolo[4,3-a]pyrazin-8-amine dihydrochloride In dimethyl sulfoxide at 50℃; Inert atmosphere;	1.36.2 Step 2: (3S,4/?)-3-fluoro-4-methylbenzyl 4-(([l,2,4]triazolo[4,3-a]pyrazin-8-ylamino)methyl)-3- fluoropiperidine-l-carboxylate Step 2: (3S,4/?)-3-fluoro-4-methylbenzyl 4-(([l,2,4]triazolo[4,3-a]pyrazin-8-ylamino)methyl)-3- fluoropiperidine-l-carboxylate M [0283] To a stirred solution of (3-fluoro-4-methylphenyl)methanol (127 mg, 0.91 mmol) in DMSO (3 mL) was added CDI (136 mg, 0.84 mmol) at room temperature. After stirring for 1 h, N-(((3S,4R)-3- fluoropiperidin-4-yl)methyl)-[l,2,4]triazolo[4,3-a]pyrazin-8-amine hydrochloride (300 mg, 0.7 mmol) was added, and the resulting mixture was heated to 50 °C under N2 atmosphere. After stirring overnight, the mixture was diluted with EtOAc. The organic layer was washed with water, brine, dried over Na2S04 and concentrated. The concentrate was purified by column chromatography over silica gel (DCM/MeOH = 40/1) to afford the title compound as a white powder (115 mg, 30%). MS (ESI) calcd for C20H22F2N6O2: 416.2 ; found: 417.3 [M+H]. *H NM R (400 M Hz, CD3OD) δ 9.09 (s, 1H), 7.70 (d, J = 4.8 Hz, 1H), 7.30 (d, J = 4.8 Hz, 1H), 7.21 (t, J = 8.0 Hz, 1H), 7.09-7.04 (m, 2H), 5.10 (br s, 2H), 4.87-4.75 (m, 1H), 4.51-4.41 (m, 1H), 4.29-4.20 (m, 1H), 3.69-3.53 (m, 2H), 3.16-2.83 (m, 2H), 2.27 (s, 3H), 2.26-2.14 (m, 1H), 1.68-1.55 (m, 2H).

Reference： [1]Current Patent Assignee: RUGEN HOLDINGS (CAYMAN) LTD - WO2016/100349, 2016, A2 Location in patent: Paragraph 0283

15
N-(((3S,4R)-3-fluoropiperidin-4-yl)methyl)-[1,2,4]triazolo[4,3-a]pyrazin-8-amine dihydrochloride [ No CAS ]
[ 192702-79-7 ]
(3S,4R)-3-fluoro-4-methylbenzyl 4-(([1,2,4]triazolo[4,3-a]pyrazin-8-ylamino)methyl)-3-fluoropiperidine-1-carboxylate methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: dimethyl sulfoxide / 1 h / 20 °C 1.2: 50 °C / Inert atmosphere 2.1: methanol; dichloromethane / 0.5 h

Reference： [1]Current Patent Assignee: RUGEN HOLDINGS (CAYMAN) LTD - WO2016/100349, 2016, A2

16
C₁₄H₁₇ClN₂O [ No CAS ]
[ 192702-79-7 ]
C₂₂H₂₅FN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In toluene at 150℃; for 0.5h; Microwave irradiation;

Reference： [1]Lee, Na-Ra; Gujarathi, Satheesh; Bommagani, Shobanbabu; Siripurapu, Kiranbabu; Zheng, Guangrong; Dwoskin, Linda P. [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 3, p. 471 - 476]

17
[ 192702-79-7 ]
2-(3-fluoro-4-methylbenzyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: phosphorus tribromide / diethyl ether / 0 - 20 °C 2: N,N-dimethyl-formamide / 100 °C